JPH085814B2 - Styrene purification method - Google Patents
Styrene purification methodInfo
- Publication number
- JPH085814B2 JPH085814B2 JP62114187A JP11418787A JPH085814B2 JP H085814 B2 JPH085814 B2 JP H085814B2 JP 62114187 A JP62114187 A JP 62114187A JP 11418787 A JP11418787 A JP 11418787A JP H085814 B2 JPH085814 B2 JP H085814B2
- Authority
- JP
- Japan
- Prior art keywords
- styrenes
- hydrogenation
- reaction
- catalyst
- styrene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】 （ｉ）発明の目的 〔産業上の利用分野〕 本発明は、スチレン類の精製方法に関するものであ
る。詳しくは、本発明は、スチレン類中に含有される高
不飽和不純物、即ち、フェニルアセチレン等のアセチレ
ン類及びジオレフィン類を選択的に水素添加して除去す
る方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION (i) Object of the Invention [Field of Industrial Application] The present invention relates to a method for purifying styrenes. More particularly, the present invention relates to a method for selectively hydrogenating and removing highly unsaturated impurities contained in styrene, that is, acetylenes such as phenylacetylene and diolefins.
スチレン類はポリマー原料として広く用いられてい
る。しかし、スチレン類を重合させてポリマーを製造す
る場合に、重合特性にバラツキがあり、安定した品質の
ポリマー製品が得られない問題点があった。Styrenes are widely used as a polymer raw material. However, when a polymer is produced by polymerizing styrenes, there is a problem in that the polymerization characteristics vary, and a polymer product of stable quality cannot be obtained.
その原因は、本発明者等の知見によれば、エチルベン
ゼン類の脱水素反応によって得られるスチレン類につい
ては、その反応において用いた触媒特性、反応形式、プ
ラントの運転条件等によって、高不飽和不純物、すなわ
ちフェニルアセチレン等のアセチレン類、ジオレフィン
類などの含有量が大巾に変動し、これらの高不飽和不純
物がスチレン類の重合時に重合抑制剤として働くことに
よることが判った。According to the findings of the present inventors, the cause is that styrenes obtained by the dehydrogenation reaction of ethylbenzenes are highly unsaturated impurities depending on the catalyst characteristics used in the reaction, the reaction format, the operating conditions of the plant, etc. That is, it was found that the contents of acetylenes such as phenylacetylene, diolefins, etc. fluctuate widely, and these highly unsaturated impurities act as a polymerization inhibitor during the polymerization of styrenes.
従来、スチレン類に含有される高不飽和不純物の除去
に関する文献等はあまり見当らないが、特公昭48-16497
号公報には、ニッケル５％以上、及びクロム、マンガ
ン、鋼の１種以上をニッケルに対して50％以下含有せし
めた固体多元触媒を特定の有機硫黄化合物で処理した触
媒を用いて、スチレン類を水素添加処理し、含有されて
いるフェニルアセチレンを選択低に水素添加して除く記
載がある。しかし、同公報に記載の水素添加処理は、液
空間速度がわずか５hr-1程度であることからして、かか
る方法はフェニルアセチレンを選択的に水素添加して除
くことができても、工業的に有利に実施できる方法では
ない。Conventionally, there are not many documents on removal of highly unsaturated impurities contained in styrenes, but Japanese Patent Publication No.
Japanese Patent Laid-Open Publication No. 2005-242242 discloses a styrene compound obtained by treating a solid multi-component catalyst containing 5% or more of nickel and 50% or less of one of chromium, manganese, and steel with respect to nickel, treated with a specific organic sulfur compound. Is hydrogenated and the contained phenylacetylene is selectively hydrogenated to be removed. However, since the hydrogenation treatment described in the publication has a liquid hourly space velocity of only about 5 hr -1 , even if such a method can selectively remove phenylacetylene by hydrogenation, it is industrially possible. It is not a method that can be implemented advantageously.
本発明者等は、既に、スチレン類を水素添加触媒の存
在下で水素添加処理をして含有される高不飽和不純物を
選択的に水素添加して除去する方法において、該水素添
加反応における反応温度を60〜120℃に保つことを特徴
とするスチレン類の精製方法を発明し、特許出願してい
る（特許出願 昭60-291015号）。しかしながら、この
方法では、反応温度を60℃より低くして反応を行なう
と、反応液中に含まれる水分により触媒が被毒され、全
く失活してしまうという問題点がある。The present inventors have already conducted a hydrogenation treatment of styrenes in the presence of a hydrogenation catalyst to selectively hydrogenate and remove highly unsaturated impurities contained in the hydrogenation reaction. He invented a method for purifying styrenes, which is characterized by keeping the temperature at 60 to 120 ° C, and applied for a patent (patent application Sho 60-291015). However, this method has a problem that when the reaction is carried out at a reaction temperature lower than 60 ° C., the catalyst is poisoned by the water contained in the reaction solution and is completely deactivated.
（ii）発明の構成 〔問題点を解決するための手段〕 本発明者等は、前記の問題点を解決するために更に鋭
意検討を重ねた結果、高不飽和不純物、特にフェニルア
セチレン等のアセチレン類を水素添加処理するに当り、
該水素添加反応系に供給する液中の水分量を2000wt・pp
m以下に規制して反応を行なえば、反応温度が60℃より
低い条件においても触媒は失活することなく、安定した
活性が得られることを見出し、本発明を完成するに至っ
た。(Ii) Configuration of the Invention [Means for Solving the Problems] The inventors of the present invention have made further diligent studies to solve the above problems, and as a result, highly unsaturated impurities, particularly acetylene such as phenylacetylene. When hydrogenating
The amount of water in the liquid supplied to the hydrogenation reaction system is 2000 wt.pp
It was found that stable reaction can be obtained without deactivating the catalyst even when the reaction temperature is lower than 60 ° C. when the reaction is carried out with the m controlled to m or less, and the present invention has been completed.
即ち、本発明のスチレン類の精製方法は、１）スチレ
ン類を水素添加触媒の存在下で水素添加処理して含有さ
れる高不飽和不純物を選択的に水素添加して除去する方
法において、該水素添加反応系に供給される該スチレン
類を含む原料中の水分含量を2000重量ppm以下に保ち且
つ該水素添加反応における反応温度を０℃〜120℃の範
囲に保つことを特徴とするスチレン類の精製方法であ
る。That is, the method for purifying styrenes according to the present invention is 1) a method for selectively hydrogenating and removing highly unsaturated impurities contained by hydrogenating styrenes in the presence of a hydrogenation catalyst, Styrenes characterized in that the water content in the raw material containing the styrenes supplied to the hydrogenation reaction system is kept at 2000 ppm by weight or less and the reaction temperature in the hydrogenation reaction is kept in the range of 0 ° C to 120 ° C. Is a purification method.
（発明の具体的説明） スチレン類 本発明の精製方法の対象となるスチレン類とは、スチ
レン、ｐ−メチルスチレン、ビニルトルエン、ｐ−ｔ−
ブチルスチレン、ジビニルベンゼン及びこれらの少なく
とも１種を含有する組成物をいう。(Detailed Description of the Invention) Styrenes Styrenes that are the subject of the purification method of the present invention include styrene, p-methylstyrene, vinyltoluene, pt-
It refers to butylstyrene, divinylbenzene and a composition containing at least one of them.
かかるスチレン類は、通常、エチルベンゼン、ｐ−メ
チルエチルベンゼン、エチルトルエン、ｐ−ｔ−ブチル
エチルベンゼン、ジエチルベンゼン等の少なくとも１種
のエチルベンゼン類を脱水素触媒、たとえばFe-Ce-Kを
主成分とする触媒（特開昭49-120887号、同49-120888
号、同53-129190号、及び同53-129191号の各公報等参
照）、又はFe-Cr-Kを主成分とする触媒等の種々の脱水
素触媒の存在下で脱水素反応をさせて得られる反応生成
物、又は同反応生成物の蒸留分離によって得られる留分
等である。Such styrenes are usually dehydrogenation catalysts of at least one ethylbenzene such as ethylbenzene, p-methylethylbenzene, ethyltoluene, pt-butylethylbenzene, and diethylbenzene, for example, a catalyst containing Fe-Ce-K as a main component. (JP-A-49-120887 and 49-120888
No., No. 53-129190, and No. 53-129191), or the dehydrogenation reaction in the presence of various dehydrogenation catalysts such as Fe-Cr-K-based catalysts. It is the reaction product obtained or a fraction obtained by distillation separation of the reaction product.
上記のような方法で得られるスチレン類には、フェニ
ルアセチレン等のアセチレン類、及びジオレフィン類が
含まれている。スチレン類中に含有されるかかる高不飽
和不純物の含有量は、製造条件等によっても異なるが、
アセチレン類が10〜1000ppm（重量）程度、ジオレフィ
ン類が５〜500ppm（重量）程度である。The styrenes obtained by the above method include acetylenes such as phenylacetylene and diolefins. The content of such highly unsaturated impurities contained in styrenes varies depending on the production conditions, etc.,
Acetylenes are about 10 to 1000 ppm (weight) and diolefins are about 5 to 500 ppm (weight).
ここで、本発明の水素添加反応系に供給される該スチ
レン類を含む原料中の水分含量は2000重量ppm以下、好
ましくは1700重量ppm以下、最も好ましくは1500重量ppm
以下に抑えることが必要である。原料中の水分含量が20
00重量ppmを越えると触媒が被毒され、短期間にアセチ
レン類を水素添加する能力が著しく低下し、実用に耐え
なくなる。Here, the water content in the raw material containing the styrenes supplied to the hydrogenation reaction system of the present invention is 2000 wtppm or less, preferably 1700 wtppm or less, and most preferably 1500 wtppm.
It is necessary to keep below. The water content in the raw material is 20
If it exceeds 00 ppm by weight, the catalyst is poisoned and the ability to hydrogenate acetylenes in a short period of time is significantly reduced, making it unusable for practical use.
その理由についての詳細は、完全には明らかになって
いないが、 触媒表面への水の親和力が強く、触媒表面を水が覆
ってしまうこと 触媒が水により酸化されてしまうこと などが考えられている。Although the details of the reason have not been completely clarified, it is considered that water has a strong affinity for the catalyst surface and that the water covers the catalyst surface and that the catalyst is oxidized by water. There is.
なお、該スチレン類をそのまま原料として反応系へ供
給する場合には、該スチレン類中の水分含量を上記の値
に規制することが必要であるが、該スチレン類を他の炭
化水素等で希釈して反応系へ供給する場合には炭化水素
等を含めた原料全体の水分含量を上記の値に規制するこ
とが必要である。When the styrenes are directly supplied to the reaction system as a raw material, it is necessary to regulate the water content in the styrenes to the above value, but the styrenes are diluted with other hydrocarbons or the like. Then, when supplying to the reaction system, it is necessary to regulate the water content of the entire raw material including hydrocarbons to the above value.
水素 本発明における水素添加反応系への水素の供給量は、
目的の高不飽和不純物の水素添加に必要な水素量の１〜
100倍量程度である。供給する水素量が多すぎるとスチ
レン等の有用成分が水素添加されてロスとなり、その収
量が低下する。Hydrogen The amount of hydrogen supplied to the hydrogenation reaction system in the present invention is
1 to 1 of the amount of hydrogen required for hydrogenation of the target highly unsaturated impurities
It is about 100 times the amount. If the amount of hydrogen supplied is too large, useful components such as styrene will be hydrogenated and will be lost, reducing the yield.
水素添加触媒 本発明の精製方法で使用する水素添加触媒は、水素添
加触媒能を有するものであればよい。好ましいその触媒
は白金族金属を触媒成分として含有する触媒である。こ
の種の水素添加触媒は、通常、その触媒成分が適当な担
体に担持されており、その触媒成分の担持量は通常、0.
01〜１重量％、好ましくは0.05〜0.5重量％である。ま
た、その担体としては、耐熱性の無機化合物担体、たと
えばアルミナ、シリカなどの合成ゲル担体、或いはケイ
ソウ土、多孔性粘土などの天然無機物担体等があげられ
る。Hydrogenation Catalyst The hydrogenation catalyst used in the purification method of the present invention may be any one having hydrogenation catalytic ability. The preferred catalyst is a catalyst containing a platinum group metal as a catalyst component. In this type of hydrogenation catalyst, the catalyst component is usually supported on an appropriate carrier, and the amount of the catalyst component supported is usually 0.1.
It is from 01 to 1% by weight, preferably from 0.05 to 0.5% by weight. Examples of the carrier include heat-resistant inorganic compound carriers, for example, synthetic gel carriers such as alumina and silica, and natural inorganic carrier such as diatomaceous earth and porous clay.
反応温度 本発明の精製方法においては、その水素添加反応を０
℃〜120℃、好ましくは10℃〜100℃、最も好ましくは20
℃〜90℃の範囲で行なうことが必要である。反応温度が
高過ぎると、スチレン等の有用なスチレン類迄が水素添
加されてロスとなるし、一方、反応温度が余り低過ぎる
と目的の高不飽和不純物を有効に水素添加して除くこと
が出来なくなる。Reaction temperature In the purification method of the present invention, the hydrogenation reaction is
℃ ~ 120 ℃, preferably 10 ℃ ~ 100 ℃, most preferably 20
It is necessary to perform in the range of ℃ ~ 90 ℃. If the reaction temperature is too high, useful styrenes such as styrene will be hydrogenated, resulting in loss.On the other hand, if the reaction temperature is too low, the desired highly unsaturated impurities can be effectively hydrogenated and removed. I can't.
又、上記反応温度域においても、反応系へ供給する原
料中の水分含量が2000重量ppmを越えると、触媒が被毒
され、活性を失う。Even in the above reaction temperature range, when the water content in the raw material supplied to the reaction system exceeds 2000 ppm by weight, the catalyst is poisoned and loses its activity.
反応圧力 本発明における水素添加反応の全圧は、通常、常圧〜
加圧下、好ましくは常圧〜10kg/cm2Ｇである。Reaction Pressure The total pressure of the hydrogenation reaction in the present invention is usually atmospheric pressure to
Under pressure, preferably atmospheric pressure to 10 kg / cm 2 G.
空間速度 本発明の水素添加反応は、バッチ方式により行なわせ
ることができるし、所定温度に保たれた触媒層へスチレ
ン類及び水素を連続的に供給して反応させる連続方式に
よっても実施することができる。連続方式で反応させる
場合の触媒層へのスチレン類の供給速度は、液空間速度
（LHSV）で１〜500hr-1、好ましくは10〜300hr-1であ
る。同速度が高すぎるとフェニルアセチレン等の高不飽
和不純物の転化率が低下して、充分に除去できなくなる
し、同速度が低くすぎるとスチレン等の有用なスチレン
類が水素添加されてロスになる。Space Velocity The hydrogenation reaction of the present invention can be carried out by a batch system, or can also be carried out by a continuous system in which styrenes and hydrogen are continuously supplied to a catalyst layer kept at a predetermined temperature to react. it can. The feed rate of the styrene to the catalyst layer when the reaction in a continuous method, 1~500hr -1 at a liquid hourly space velocity (LHSV), preferably 10~300hr -1. If the rate is too high, the conversion rate of highly unsaturated impurities such as phenylacetylene will decrease, and it will not be able to be sufficiently removed.If the rate is too low, useful styrenes such as styrene will be hydrogenated and will be lost. .
以下に、触媒製造例、実施例及び比較例をあげてさら
に詳述する。これらの例に記載のppm及び％は特に記載
しない限り重量基準による。The catalyst production examples, examples and comparative examples will be described in more detail below. Unless otherwise specified, ppm and% described in these examples are based on weight.
触媒製造例 3mmφ×3mmの円柱型に成形したγ−アルミナに、濃度
0.6重量％の塩化パラジウム水溶液を含浸させ、110℃で
１昼夜乾燥させた。Example of catalyst production The concentration of γ-alumina molded into a 3 mmφ × 3 mm cylindrical shape was
A 0.6% by weight aqueous palladium chloride solution was impregnated and dried at 110 ° C. for one day.
次いで、その乾燥物を水素気流下で400℃の温度で16
時間還元処理して、組成がPd（0.3％）／γ−Al2O3の水
素添加触媒を得た。The dried product is then stored under a stream of hydrogen at a temperature of 400 ° C for 16
After a time reduction treatment, a hydrogenation catalyst having a composition of Pd (0.3%) / γ-Al 2 O 3 was obtained.
実施例−１ 上記の様にして調製した触媒50gを直径20mm、長さ50c
mのステンレス反応管に充填した。この反応管を40℃に
保ち、これにエチルベンゼンの脱水素反応で得られた粗
スチレン留分（スチレン65wt％、エチルベンゼン31wt
％、ベンゼン1.5wt％、トルエン2.5wt％、フェニルアセ
チレン50〜150wtppm、水100〜250wtppm含有）を1000cc/
hr、反応圧力4kg/cm2Ｇ、H2／フェニルアセチレン1.5モ
ル／モルの条件で連続的に供給した。供給後８時間目の
フェニルアセチレンの水添率は62％、20日目、100日目
の水添率はそれぞれ59％、60％であり、安定した活性が
得られた。Example 1 50 g of the catalyst prepared as described above was used to obtain a diameter of 20 mm and a length of 50 c.
It was filled in a stainless steel reaction tube of m. This reaction tube was kept at 40 ° C, and the crude styrene fraction obtained by the dehydrogenation reaction of ethylbenzene (styrene 65 wt%, ethylbenzene 31 wt%
%, Benzene 1.5 wt%, toluene 2.5 wt%, phenylacetylene 50 to 150 wtppm, water 100 to 250 wtppm) 1000 cc /
It was continuously fed under the conditions of hr, reaction pressure 4 kg / cm 2 G, H 2 / phenylacetylene 1.5 mol / mol. The hydrogenation rates of phenylacetylene 8 hours after the supply were 62%, and the hydrogenation rates on the 20th and 100th days were 59% and 60%, respectively, and stable activity was obtained.
実施例−２ 反応管を20℃に保った以外は実施例−１と同様の条件
で反応を行なった。粗スチレンの供給後８時間目のフェ
ニルアセチレンの水添率は57％、20日目、40日目の水添
率はそれぞれ59％、57％と安定した活性が得られた。Example-2 The reaction was carried out under the same conditions as in Example-1, except that the reaction tube was kept at 20 ° C. Eight hours after the supply of crude styrene, the hydrogenation rate of phenylacetylene was 57%, and the hydrogenation rates on the 20th and 40th days were 59% and 57%, respectively, showing stable activity.
比較例 粗スチレン留分中の水分量を2500wtppmにしたこと以
外は実施例−２と同一の条件で反応を行なった。粗スチ
レンの供給後６時間目にはフェニルアセチレンの水添率
は63％であったが24時間目、48時間目にはそれぞれ20
％、０％となり、著しい活性低下が認められた。Comparative Example The reaction was carried out under the same conditions as in Example-2 except that the amount of water in the crude styrene fraction was 2500 wtppm. The hydrogenation rate of phenylacetylene was 63% at 6 hours after supplying the crude styrene, but it was 20% at 24 hours and 48 hours respectively.
%, 0%, and a remarkable decrease in activity was observed.
（iii）発明の効果 本発明の精製方法によれば、スチレン類中に含まれる
フェニルアセチレン等の不純物を、高い水素添加選択率
で安定して除去することができ、その際にスチレン等の
有用成分の水素添加による消耗が少ない。(Iii) Effects of the Invention According to the purification method of the present invention, impurities such as phenylacetylene contained in styrenes can be stably removed with a high hydrogenation selectivity, at which time useful styrene and the like are useful. Less consumption due to hydrogen addition of components.
従って、本発明により、重合特性にバラツキがなく、
品質の安定したポリマー製品を得るのに適する精製スチ
レン類を有利に製造することが出来る。Therefore, according to the present invention, there is no variation in the polymerization characteristics,
Purified styrenes suitable for obtaining stable quality polymer products can be advantageously produced.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 江川 一雄 茨城県鹿島郡神栖町東和田17番地 三菱油 化株式会社鹿島事業所内 (72)発明者 清水 正 茨城県鹿島郡神栖町東和田17番地 三菱油 化株式会社鹿島事業所内 (56)参考文献 特開 昭62−87535（ＪＰ，Ａ) ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Kazuo Egawa 17 Towada, Kamisu-cho, Kashima-gun, Ibaraki Prefecture Kashima Plant, Mitsubishi Petrochemical Co., Ltd. (72) Tadashi Shimizu 17 Towada, Kamisu-cho, Kashima-gun, Ibaraki Mitsubishi Petrochemical Kashima Plant Co., Ltd. (56) References JP-A-62-87535 (JP, A)
Claims (1)
添加処理して含有される高不飽和不純物を選択的に水素
添加して除去する方法において、該水素添加反応系に供
給される該スチレン類を含む原料中の水分含量を2000重
量ppm以下に保ち且つ該水素添加反応における反応温度
を０℃〜120℃の範囲に保つことを特徴とするスチレン
類の精製方法。1. A method for selectively hydrogenating and removing highly unsaturated impurities contained by subjecting styrenes to hydrogenation treatment in the presence of a hydrogenation catalyst, the method comprising supplying the hydrogenation reaction system to the hydrogenation reaction system. A method for purifying styrenes, characterized in that the water content in a raw material containing styrenes is kept at 2000 ppm by weight or less and the reaction temperature in the hydrogenation reaction is kept in the range of 0 ° C to 120 ° C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62114187A JPH085814B2 (en) | 1987-05-11 | 1987-05-11 | Styrene purification method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62114187A JPH085814B2 (en) | 1987-05-11 | 1987-05-11 | Styrene purification method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63277639A JPS63277639A (en) | 1988-11-15 |
| JPH085814B2 true JPH085814B2 (en) | 1996-01-24 |
Family
ID=14631375
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62114187A Expired - Fee Related JPH085814B2 (en) | 1987-05-11 | 1987-05-11 | Styrene purification method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH085814B2 (en) |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53103428A (en) * | 1977-02-21 | 1978-09-08 | Uop Inc | Method of dehydrogenating alkyl aromatic hydrocarbon |
| JPS59196742A (en) * | 1983-04-22 | 1984-11-08 | Showa Denko Kk | Regeneration of selectively hydrocracking catalyst |
| JPS59216838A (en) * | 1983-05-25 | 1984-12-06 | Mitsubishi Petrochem Co Ltd | Purification of styrene-containing composition by selective hydrogenation |
| JPS604139A (en) * | 1983-06-22 | 1985-01-10 | Showa Denko Kk | Selective hydrogenation process |
| JPS6013724A (en) * | 1983-07-01 | 1985-01-24 | Mitsubishi Petrochem Co Ltd | Purification of styrenes |
| JPS60132652A (en) * | 1983-12-22 | 1985-07-15 | Showa Denko Kk | Regeneration of selective hydrogenating catalyst |
| JPH0645561B2 (en) * | 1985-02-21 | 1994-06-15 | 旭化成工業株式会社 | Styrene-containing material purification method |
| JPS6287535A (en) * | 1985-10-15 | 1987-04-22 | Mitsubishi Petrochem Co Ltd | Purification of styrene or such |
| DE3917064A1 (en) * | 1989-05-26 | 1990-11-29 | Bosch Gmbh Robert | SHOCK ABSORBER II |
-
1987
- 1987-05-11 JP JP62114187A patent/JPH085814B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63277639A (en) | 1988-11-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0273900B1 (en) | Improved process for the selective hydrogenation of acetylenes | |
| KR20020059441A (en) | Carrier Catalytic Converter for the Selective Hydrogenation of Alkines and Dienes | |
| KR100588178B1 (en) | Process for the hydrogenation of phenyl acetylene in a styrene-containing medium with the aid of a catalyst | |
| US4257877A (en) | Selective hydrogenation process | |
| US5905178A (en) | Removal of α-methyl styrene from cumene | |
| US3381048A (en) | Isomerization of xylene isomers | |
| JPH085814B2 (en) | Styrene purification method | |
| US4174355A (en) | Process for removing α-acetylenes from diolefins | |
| CA2315101A1 (en) | Meta-xylene production process | |
| JPS6013724A (en) | Purification of styrenes | |
| JPH085815B2 (en) | Styrene purification method | |
| US4390741A (en) | Process for the purification of diisopropenylbenzene | |
| JPH0566931B2 (en) | ||
| JPH0745419B2 (en) | Styrene purification method | |
| JP2640449B2 (en) | Purification method of styrenes | |
| US4266086A (en) | Process for removing α-acetylenes from diolefins | |
| EP2223987A1 (en) | Purification of an aromatic fraction containing acetylenes by selective hydrogenation of the acetylenes | |
| JPS59216838A (en) | Purification of styrene-containing composition by selective hydrogenation | |
| CA1290354C (en) | Process for the selective hydrogenation of alkynes | |
| JPH05310611A (en) | Production of 2-methylnaphthalene | |
| JPH0645561B2 (en) | Styrene-containing material purification method | |
| JPS62149634A (en) | Purification of styrene | |
| JP2000191557A (en) | Purification of styrenes | |
| EP0155223A1 (en) | Process for the synthesis and purification diisopropenylbenzene | |
| JPS6272634A (en) | Purification of styrene compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |